Acetic Acid → HCID 14851951, compound

HRID 1032773Notes

Reaction equation

HRID 1032773 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[CH:7]1[C:17]2[C:16](=[O:18])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=[O:23])[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.C(Br)C#C.C(O)(=O)C>CN(C)C=O.O>[CH2:3]([N:12]1[C:13](=[O:23])[C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16](=[O:18])[C:17]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]1=2)[C:2]#[CH:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7842Propargyl bromideHCID 708365H-Dibenz(b,e)azepine-6,11-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 14851951HCID 14851951, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

potassium tert.-butoxide, 2.5 g, was added to a suspension of 4.5 g of 5H-dibenz[b,e]azepine-6,11-dione in 50 ml of dimethylformamide. After stirring under nitrogen for 30 minutes, 2 ml of propargyl bromide was added and stirring was continued for I hour at room temperature. The reaction mixture was acidified with acetic acid and diluted with water. The precipitate was filtered off and sucked dry. The solids were dissolved in methylene chloride. The solution was dried and evaporated and the residue was chromatographed over 120 g of silica gel using methylene chloride. The combined clean fractions containing product were evaporated and the residue was crystallized from ether/hexane to give colorless crystals of 5-(2-propynyl)-5H-dibenz[b,e]azepine-6,11-dione with m.p. 117°-118°.

Workup

  1. stirringstirring
  2. customwas continued for I hour at room temperature
  3. filtrationThe precipitate was filtered off
  4. customsucked dry
  5. dissolutionThe solids were dissolved in methylene chloride
  6. customThe solution was dried
  7. customevaporated
  8. customthe residue was chromatographed over 120 g of silica gel
  9. additionThe combined clean fractions containing product
  10. customwere evaporated
  11. customthe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-27e76e53fbab471ebbd55c48a53ff7e3
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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